In 2010, I began my PhD project in New Zealand. My study focused on the identity work of Filipino migrants in Auckland as constructed in their discourses on social media. It was mainly an interpretive project guided by the methods involved in discourse-centered online ethnography and the framework of multimodal discourse analysis. My premise in the research was-notwithstanding the practical significance of Internet-based communication and information technologies in the lives of migrants who desire to maintain contact and sustain relationships in the former home-these new media formats also act as performative spaces of their migrant selves and migrant lives. In this case study, I do not discuss the specific results of the research. Rather, my particular concern here is a seemingly ignored aspect of the interpretive process–guessing. Although not considered a method, per se, in my research, I realized how important it is to acknowledge that guessing plays a crucial role in the attempt at understanding, which is the primary goal of any hermeneutic task. In this case study, I expand the discussion of the act of guessing to other related concepts such as abduction, intuition, thin-slicing, and the Filipino concept of datíng and discuss their value in research work. I also advance the idea that these “pre-analytical” moments of knowing are important considerations in research, although intuition is not right all the time.